1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones

[Image: see text] 1,3-Diamine-derived catalysts were designed, synthesized, and used in asymmetric Mannich reactions of ketones. The reactions catalyzed by one of the 1,3-diamine derivatives in the presence of acids afforded the Mannich products with high enantioselectivities under mild conditions....

Descripción completa

Detalles Bibliográficos
Autores principales: Garg, Yuvraj, Osborne, James, Vasylevskyi, Serhii, Velmurugan, Nivedha, Tanaka, Fujie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407930/
https://www.ncbi.nlm.nih.gov/pubmed/37460110
http://dx.doi.org/10.1021/acs.joc.3c01051
_version_ 1785086073461800960
author Garg, Yuvraj
Osborne, James
Vasylevskyi, Serhii
Velmurugan, Nivedha
Tanaka, Fujie
author_facet Garg, Yuvraj
Osborne, James
Vasylevskyi, Serhii
Velmurugan, Nivedha
Tanaka, Fujie
author_sort Garg, Yuvraj
collection PubMed
description [Image: see text] 1,3-Diamine-derived catalysts were designed, synthesized, and used in asymmetric Mannich reactions of ketones. The reactions catalyzed by one of the 1,3-diamine derivatives in the presence of acids afforded the Mannich products with high enantioselectivities under mild conditions. In most cases, bond formation occurred at the less-substituted α-position of the ketone carbonyl group. Our results indicate that the primary and the tertiary amines of the 1,3-diamine derivative cooperatively act for the catalysis.
format Online
Article
Text
id pubmed-10407930
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-104079302023-08-09 1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones Garg, Yuvraj Osborne, James Vasylevskyi, Serhii Velmurugan, Nivedha Tanaka, Fujie J Org Chem [Image: see text] 1,3-Diamine-derived catalysts were designed, synthesized, and used in asymmetric Mannich reactions of ketones. The reactions catalyzed by one of the 1,3-diamine derivatives in the presence of acids afforded the Mannich products with high enantioselectivities under mild conditions. In most cases, bond formation occurred at the less-substituted α-position of the ketone carbonyl group. Our results indicate that the primary and the tertiary amines of the 1,3-diamine derivative cooperatively act for the catalysis. American Chemical Society 2023-07-17 /pmc/articles/PMC10407930/ /pubmed/37460110 http://dx.doi.org/10.1021/acs.joc.3c01051 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Garg, Yuvraj
Osborne, James
Vasylevskyi, Serhii
Velmurugan, Nivedha
Tanaka, Fujie
1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones
title 1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones
title_full 1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones
title_fullStr 1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones
title_full_unstemmed 1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones
title_short 1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones
title_sort 1,3-diamine-derived catalysts: design, synthesis, and the use in enantioselective mannich reactions of ketones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407930/
https://www.ncbi.nlm.nih.gov/pubmed/37460110
http://dx.doi.org/10.1021/acs.joc.3c01051
work_keys_str_mv AT gargyuvraj 13diaminederivedcatalystsdesignsynthesisandtheuseinenantioselectivemannichreactionsofketones
AT osbornejames 13diaminederivedcatalystsdesignsynthesisandtheuseinenantioselectivemannichreactionsofketones
AT vasylevskyiserhii 13diaminederivedcatalystsdesignsynthesisandtheuseinenantioselectivemannichreactionsofketones
AT velmurugannivedha 13diaminederivedcatalystsdesignsynthesisandtheuseinenantioselectivemannichreactionsofketones
AT tanakafujie 13diaminederivedcatalystsdesignsynthesisandtheuseinenantioselectivemannichreactionsofketones

Ejemplares similares